In the field of production of optically active amines, many asymmetric reactions, including asymmetric reduction, have been developed, and many asymmetric reactions have been reported which use asymmetric metal complexes having optically active phosphine ligands. Meanwhile, for example, there are many documents reporting that complexes in each of which an optically active nitrogen compound is coordinated to a transition metal, such as ruthenium, rhodium, or iridium, have excellent performance as catalysts for asymmetric synthesis reactions (see Chem Rev. (1992), p. 1051, J. Am. Chem. Soc. 117 (1995), p. 7562, J. Am. Chem. Soc. 118 (1996), p. 2521, and J. Am. Chem. Soc. 118 (1996), p. 4916). Especially, synthesis of optically active amines by hydrogenation reaction has been reported recently (see J. Am. Chem. Soc. 133 (2011), p. 9878, and Angew. Chem. Int. Ed 51 (2012), p. 5706).
However, the conventional asymmetric synthesis methods using these complexes may result in insufficient catalytic activity or insufficient enantiomeric excesses, when certain reaction substrates are used. Hence, further development of such a complex has been demanded. Wills et al. have reported a complex in which the nitrogen atom in one of the diamine moieties is methylated. However, the reaction is limited to the hydrogen transfer reaction, and the element coordinated to ruthenium is a halogen (see Organic Letters (2009) vol. 11, No. 4, p 847).